Hydrochloric Acid → [4-(4-Fluorobenzoyl)phenyl]-(4-fluorophenyl)methanone

HRID 1885657Notes

Reaction equation

HRID 1885657 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl>>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:5]([C:6]2[CH:14]=[CH:13][C:9]([C:10](=[O:11])[C:21]3[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=3)=[CH:8][CH:7]=2)=[O:15])=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7488Terephthaloyl chlorideHCID 10008FluorobenzeneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11141804[4-(4-Fluorobenzoyl)phenyl]-(4-fluorophenyl)methanoneYield 88%

Procedure

Anhydrous aluminum chloride (80.0 g, 0.60 mol) was added to a stirred solution of terephthaloyl chloride (50.8 g, 0.25 mol) dissolved in fluorobenzene (235 ml, 2.5 mol) over a 10-15 minute period. The mixture was stirred at room temperature for one hour and then maintained at 70°-80° C. for four hours. After cooling, the reaction mixture was poured onto approximately 1000 g of ice containing 100 ml of concentrated hydrochloric acid. The resulting suspension was separated by decantation and washed several times with water. The organic layer was distilled to remove excess fluorobenzene and the solid residue collected by filtration, washed with water, and dried at 100° C. The crude solid was recrystallized from approximately 2000 ml of toluene to afford 70.7 g (88% yield) of 1,4-bis(4-fluorobenzoyl)-benzene; mp 218.5°-219.5° C.; Anal. Calcd for C20H12F2O2 : C, 74.53%; H, 3.75%; F, 11.179%. Found: C, 74.60%; H, 3.80%; F, 11.83%.

Workup

  1. temperaturemaintained at 70°-80° C. for four hours
  2. temperatureAfter cooling
  3. customThe resulting suspension was separated by decantation
  4. washwashed several times with water
  5. distillationThe organic layer was distilled
  6. customto remove excess fluorobenzene
  7. filtrationthe solid residue collected by filtration
  8. washwashed with water
  9. customdried at 100° C
  10. customThe crude solid was recrystallized from approximately 2000 ml of toluene

Sources & evidence

ORD record
ord-0896f7a069114cef8c71882a43293ed7
Source dataset
uspto-grants-1992_09
Patent number
US05145937

Reaction notes

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